KR20230175107A - Compound, Organic EL Device and Display Device - Google Patents

Abstract

According to the present invention, a compound applicable to an electron transport layer, a hole blocking layer (electron transport auxiliary layer), etc. of an organic electroluminescent device, an organic electroluminescent device using such a compound, and a display device including such an organic electroluminescent device is provided.

Description

Compound, organic electroluminescent device and display device {Compound, Organic EL Device and Display Device}

The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices, and organic electroluminescent devices and display devices containing the same.

Recently, displays using organic electroluminescent elements have been attracting attention as full-color flat displays, and are being used in display devices such as smartphones, TVs, automobiles, and VR (Virtual Reality) head-mounted devices.

An organic electroluminescent element has a structure including a pair of electrodes consisting of an anode and a cathode, and an organic material layer portion disposed between the pair of electrodes and having one or more organic compound layers. The organic material layer includes a light-emitting layer and a charge transport/injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers are being developed.

In order to further expand the application fields of displays using organic electroluminescent devices, there is a need to reduce device power consumption (lower voltage and improve external quantum efficiency) and extend lifespan. In particular, there is a demand for lower power consumption and longer lifespan of blue light-emitting devices, and to this end, various materials for electron transport/injection layers are being examined.

For example, as materials for the electron transport/injection layer, pyridine derivatives or bipyridine derivatives (Patent Document 1), benzimidazole or benzothiazole derivatives (Patent Documents 2 to 4), pyrimidine derivatives, or triazine derivatives (Patent Document 1). 5) Organic electroluminescent devices using are known.

However, in the case of these conventional electron transport/injection layer materials, further improvements are required in terms of luminous efficiency, driving voltage, and lifespan.

In particular, in conventional organic electroluminescent devices, excitons and/or holes generated in the light-emitting layer diffuse into the electron transport layer and emit light at the interface with the electron transport layer, resulting in reduced luminous efficiency and reduced lifespan.

Japanese Patent Publication No. 2003-123983 US Patent Publication 2003/215667 International Publication 2003/060956 International Publication 2008/117976 Registered Patent Publication No. 2084906

The present invention is a novel compound that has high stability and high electron mobility for electrons and can suppress the diffusion of excitons and/or holes into the electron transport layer, and an organic electroluminescence device with high efficiency, low driving voltage, and long lifespan. The purpose is to provide a device and a display device using the same.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1).

In Formula 1,

Ar ₁ is deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group , a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, a substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, a substituted or unsubstituted Is selected from the group consisting of a C ₁ -C ₃₀ alkylsilyl group, a substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group,

L ₁ to L ₃ are the same or different from each other, and each independently represents a single bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₃ -C ₃₀ heteroarylene group,

R ₁ is deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group , a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, a substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, a substituted or unsubstituted Selected from the group consisting of a C ₁ -C ₃₀ alkylsilyl group, a substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group, and a plurality of R ₁ may combine with adjacent groups to form a substituted or unsubstituted ring,

o is an integer from 0 to 7,

A and B are the same or different from each other, and are each independently deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted substituted C ₃ -C ₂₀ aralkyl group, substituted or unsubstituted C ₆ -C ₃₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₃ -C ₂₀ A heteroaralkyl group, a substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, a substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group. is selected from the group consisting of

A can be bonded to L ₂ or B by a single bond, and B can be bonded to L ₁ or A by a single bond,

m and n are each integers from 0 to 2, and m + n ≥ 1,

At least one A or B is represented by the formula 2 below,

In Formula 2 above,

Het is a C ₃ -C ₃₀ heteroaryl group containing N as a hetero atom,

L ₄ is a single bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₃ -C ₃₀ heteroarylene group.

Additionally, the present invention provides an organic electroluminescent device including such a compound in an organic material layer, and a display device including the organic electroluminescent device.

In particular, when the new compound represented by Formula 1 of the present invention is used as a material for the electron transport layer and/or the hole blocking layer (electron transport auxiliary layer), it has excellent luminous performance, low driving voltage, high efficiency and long life compared to conventional materials. It is possible to manufacture an organic electroluminescent device having a , and furthermore, to manufacture a full-color display panel with greatly improved performance and lifespan.

1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, embodiments of the present invention will be described in detail with reference to the attached drawings. In describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description will be omitted.

<Description of the compounds of the present invention>

The compound according to the present invention includes a structure represented by the following formula (1).

In Formula 1,

Ar ₁ is deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group , a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, a substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, a substituted or unsubstituted Is selected from the group consisting of a C ₁ -C ₃₀ alkylsilyl group, a substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group,

L ₁ to L ₃ are the same or different from each other, and each independently represents a single bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₃ -C ₃₀ heteroarylene group,

R ₁ is deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group , a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, a substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, a substituted or unsubstituted Selected from the group consisting of a C ₁ -C ₃₀ alkylsilyl group, a substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group, and a plurality of R ₁ may combine with adjacent groups to form a substituted or unsubstituted ring,

o is an integer from 0 to 7,

A and B are the same or different from each other, and are each independently deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted substituted C ₃ -C ₂₀ aralkyl group, substituted or unsubstituted C ₆ -C ₃₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₃ -C ₂₀ A heteroaralkyl group, a substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, a substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group. is selected from the group consisting of

A can be bonded to L ₂ or B by a single bond, and B can be bonded to L ₁ or A by a single bond,

m and n are each integers from 0 to 2, and m + n ≥ 1,

At least one A or B is represented by the formula 2 below,

In Formula 2 above,

Het is a C ₃ -C ₃₀ heteroaryl group containing N as a hetero atom,

L ₄ is a single bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₃ -C ₃₀ heteroarylene group.

Hereinafter, the substituents in the present invention will be described in detail.

The position where a substituent is not bonded to the compound described herein may be hydrogen or deuterium may be bonded thereto.

In this specification, the term “substitution” means changing the hydrogen atom bonded to the carbon atom of the compound to another substituent, and the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, 2 In the case of more than one substitution, two or more substituents may be the same or different from each other.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group; Cyano group; Phosphine oxide group; Alkyl group; alkenyl group; Alkynyl group; Cycloalkyl group; heteroalkyl group; Aryl group; heterocyclic group; Aralkyl group; heteroaralkyl group; Aralkenyl group; Alkylaryl group; alkenyl aryl group; Alkoxy group; Aryloxy group; Arylphosphine oxide group; silyl group; Alkylamine group; Aralkylamine group; Arylamine group; Alkylarylamine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroarylamine group, or substituted or unsubstituted with a substituent in which two or more of the above-exemplified substituents are linked. For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but may be, for example, 1 to 100, 1 to 80, 1 to 50, or 1 to 20. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n. -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited to these.

In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but may be, for example, 2 to 100, 2 to 80, 2 to 50, or 2 to 30. Specific examples of alkenyl groups include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, and 3-methyl. -1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl- 2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited to these. .

In the present specification, the number of carbon atoms of the alkynyl group is not particularly limited, but may be 2 to 50, 2 to 30, or 2 to 20. Specifically, the alkynyl group may be an unsaturated aliphatic hydrocarbyl group containing a triple bond such as an ethynyl group, but is not limited thereto.

In the present specification, the number of carbon atoms of the cycloalkyl group is not particularly limited, but may be 3 to 100, 3 to 60, or 3 to 30. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, Examples include, but are not limited to, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

As used herein, a heteroalkyl group or heterocycloalkyl group refers to an alkyl group or a cycloalkyl group each having one or more carbon atoms substituted by a heteroatom. The heteroatoms are selected from O, S, N, P, B, Si, and Se, preferably O, S, or N.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but may be 6 to 80, 6 to 60, 6 to 50, or 6 to 30 carbon atoms. Specific monocyclic aryl groups may include phenyl groups, biphenyl groups, and terphenyl groups, but are not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, , , , , and It can be etc. However, it is not limited to this.

In the present specification, examples of the arylphosphine oxide group include a substituted or unsubstituted monoarylphosphine oxide group, a substituted or unsubstituted diarylphosphine oxide group, or a substituted or unsubstituted triarylphosphine oxide group. . The aryl group in the arylphosphine oxide group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine oxide group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group simultaneously.

As used herein, an aralkyl group or heteroaralkyl group refers to an alkyl group substituted with an aryl group or heteroaryl group. The number of carbon atoms is not limited, but may be 3 to 20.

In the present specification, the silyl group may be represented by the formula -SiR _a R _b R _c , where R _a , R _b , and R _c are each hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No. The number of carbon atoms is not limited, but when R _a , R _b and R _c are each a substituted or unsubstituted alkyl group, the carbon number may be 1 to 30, and if they are a substituted or unsubstituted aryl group, the carbon number may be 6 to 30. In the case of a substituted or unsubstituted heteroaryl group, the number of carbon atoms may be 3 to 30.

In the present specification, the heterocyclic group is an aromatic or aliphatic heterocyclic group containing at least one of N, O, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but has 2 to 80 carbon atoms, 2 to 60 carbon atoms, or 2 to 2 carbon atoms. It could be 40. Specific examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, and triazole group. , acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, carboline group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but is not limited to these.

In the present specification, the heteroaryl group may be described as an aromatic heterocyclic group among heterocyclic groups. The number of carbon atoms is not particularly limited, but may be 3 to 30 carbon atoms. The heteroaryl group may include the structure below.

In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but may have 1 to 50 carbon atoms, 1 to 30 carbon atoms, or 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It may be possible, but it is not limited to this.

In this specification, the aryl group in the aryloxy group is the same as the example of the aryl group described above. Specifically, aryloxy groups include phenoxy, p-toryloxy, m-toryloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, and 3-biphenyl. Oxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryl Oxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy, 9-phenanthryloxy, etc. Arylthioxy groups include phenylthioxy, 2-methylphenylthioxy, and 4-tert-butylphenyl. There is a thioxy group, etc., but it is not limited thereto.

In the present specification, an alkylamine group, an aralkylamine group, an arylamine group, an alkylarylamine group, and a heteroarylamine group are amine groups substituted with an alkyl group, an aralkyl group, an aryl group, an alkylaryl group, and a heteroaryl group, respectively. Here, the description of the above-described alkyl group and aryl group may be applied to alkyl and aryl, and the description of the aromatic heterocyclic group among the above-described heterocyclic groups may be applied to the heteroaryl group. Specific examples of amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine, 4 -Methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, etc. However, it is not limited to these.

In the present specification, an arylene group refers to an aryl group having two binding positions, that is, a bivalent group. The description of the aryl group described above can be applied, except that each of these is a divalent group.

In the present specification, a heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a bivalent group. The description of the aromatic heterocyclic group described above can be applied, except that each of these is a divalent group.

In the present specification, forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means forming a condensed ring thereof.

In this specification, “adjacent group” refers to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. It can mean. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring can be interpreted as “adjacent groups”.

In the present specification, an aliphatic hydrocarbon ring refers to a non-aromatic ring consisting only of carbon and hydrogen atoms.

In the present specification, examples of aromatic hydrocarbon rings include phenyl groups, naphthyl groups, and anthracenyl groups, but are not limited to these.

As used herein, an aliphatic heterocycle refers to an aliphatic ring containing at least one of N, O, or S atoms as a heteroatom.

As used herein, an aromatic heterocycle refers to an aromatic ring containing at least one of N, O, or S atoms as a heteroatom.

In the present specification, the aliphatic ring, aromatic ring, aliphatic heterocycle, and aromatic heterocycle may be monocyclic or polycyclic.

The compound containing the structure of Formula 1 has a nitrogen-containing heteroaryl group and an aryl group connected to a specific position of the phenanthrene group, thereby producing an organic electroluminescent device with high luminous efficiency, low driving voltage, and improved device lifespan. It can be manufactured.

According to one embodiment of the present invention, at least one of Het of Formula 1 is represented by any one of Formulas 3 to 6 below.

In formulas 3 to 6,

A ₁ to A ₃₂ are the same or different from each other, are each independently N or CR ₂ , and are at least one of A ₁ to A ₆ , at least one of A ₇ to A ₁₄ , at least one of A ₁₅ to A ₂₄ , or A ₂₅ to A ₃₂ , at least one is N,

R ₂ of CR ₂ as A ₁ to A ₃₂ are the same or different from each other, and are each independently hydrogen, deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkyl group of C ₁ -C ₂₀ , a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group, substituted or unsubstituted C ₆ -C ₃₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, Substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and substituted or unsubstituted is selected from the group consisting of C ₃ -C ₃₀ heteroarylsilyl groups, and adjacent R ₂ groups may be bonded to each other to form a substituted or unsubstituted ring,

Y ₁ is O, S or CR ₃ ,

R ₃ of CR 3 as Y ₁ is hydrogen, deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy _group , substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ Cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted aralkyl group of C ₃ -C ₂₀ , substituted or unsubstituted C ₆ -C ₃₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₃ -C ₂₀ Heteroaralkyl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group. It is selected from the group consisting of, and adjacent R ₃ may be bonded to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, Ar ₁ of Formula 1 is a nitro group, a halogen group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, or a substituted Or an unsubstituted C ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, or a substituted or unsubstituted C ₃ - It is selected from the group consisting of a C ₃₀ aralkyl group and a substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group.

For example, the compounds of the present invention include the following compounds.

<Organic electroluminescent device>

Below, an organic electroluminescent device according to an embodiment of the present invention will be described in detail based on the drawings.

The organic electroluminescent device 1 shown in FIG. 1 includes an anode 110 (first electrode) installed on a substrate 100, a hole injection layer 120 installed on the anode 110, and a hole injection layer 120. ) a hole transport layer 130 installed on the hole transport layer 130, a light-emitting layer 140 installed on the hole transport layer 130, an electron transport layer 150 installed on the light-emitting layer 140, and an electron injection layer installed on the electron transport layer 150. (160) and a cathode (170, a second electrode) provided on the electron injection layer (160). In FIG. 1, the organic material layer portion including layers between the anode 110 and the cathode 170 constitutes the light emitting stack portion. Figure 1 shows a structure in which the organic material layer has one light-emitting stack, but the present invention is not limited to this and may have a plurality of light-emitting stacks.

In addition, the organic electroluminescent element 1 has the stacked structure reversed (so-called inverted element), for example, a cathode provided on the substrate 100, an electron injection layer provided on the cathode, and an electron injection layer on the electron injection layer. It may be configured to include an electron transport layer provided on the electron transport layer, a light emitting layer provided on the electron transport layer, a hole transport layer provided on the light emitting layer, a hole injection layer provided on the hole transport layer, and an anode provided on the hole injection layer.

In the organic electroluminescent device of the present invention, not all of the above layers are essential, and the minimum structural unit is composed of an anode 110, a light emitting layer 140, and a cathode 170, and a hole injection layer 120 and a hole injection layer 120. At least one of the transport layer 130, the electron transport layer 150, and the electron injection layer 160 may be omitted.

For example, in addition to the configuration of “anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode” which describes the laminate structure of the organic electroluminescent element, “anode/hole transport layer/light-emitting layer/electron transport layer/electron injection” layer/cathode”, “anode/hole injection layer/light-emitting layer/electron transport layer/electron injection layer/cathode”, “anode/hole injection layer/hole transport layer/light-emitting layer/electron injection layer/cathode”, “anode/hole injection layer/ Hole transport layer/light-emitting layer/electron transport layer/cathode”, “anode/light-emitting layer/electron transport layer/electron injection layer/cathode”, “anode/hole transport layer/light-emitting layer/electron injection layer/cathode”, “anode/hole transport layer/light-emitting layer/electron” Transport layer/cathode”, “anode/hole injection layer/light-emitting layer/electron injection layer/cathode”, “anode/hole injection layer/light-emitting layer/electron transport layer/cathode”, “anode/light-emitting layer/electron transport layer/cathode”, “anode/ It may be configured as “light emitting layer/electron injection layer/cathode”.

In addition, for the purpose of controlling the balance of the concentration of holes and electrons in the light-emitting layer 140, the area between the anode 110 and the light-emitting layer 140 (hole transport area) and between the light-emitting layer 140 and the cathode 170. A separate layer (for example, a hole blocking layer (electron transport auxiliary layer) and/or an electron blocking layer (hole transport auxiliary layer), etc.) may be added to the region (electron transport region).

In this case, the organic electroluminescent device 1 has “anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode”, “anode/hole injection layer/hole transport layer/light emitting layer/ It can have a stacked structure such as “hole blocking layer/electron transport layer/electron injection layer/cathode”, “anode/hole injection layer/hole transport layer/electron blocking layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode”, etc. there is.

Additionally, each of the above layers may be composed of a single layer or may be composed of multiple layers.

Hereinafter, the substrate 100 used to manufacture the organic electroluminescent device 1 and each layer forming the organic electroluminescent device 1 will be described in detail.

The substrate 100 is a support that supports the organic electroluminescent element 1, and glass, metal, polymer, semiconductor (silicon), etc. are usually used. The substrate 100 is formed in a plate shape, a film shape, or a sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a polymer film, a polymer sheet, etc. are used. Among them, glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferable. When manufacturing a flexible display, a glass plate (also called carrier glass) coated with a highly thermally stable and flexible polymer material (eg, polyimide) can be used as the substrate 100.

If it is a glass substrate, soda-lime glass, alkali-free glass, etc. are used, and the thickness just needs to be sufficient to maintain mechanical strength, so for example, it can be 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, and preferably 1 mm or less. Regarding the material of glass, alkali-free glass is preferable because it is better to have fewer ions eluted from the glass, but soda-lime glass coated with a barrier coating such as SiO ₂ is also commercially available and can be used. Additionally, in order to increase gas barrier properties, the substrate 100 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side. In particular, when a polymer plate, film or sheet with low gas barrier properties is used as the substrate 100, It is desirable to install a gas barrier film.

The anode 110 is an electrode that injects holes, and the anode material is preferably a material with a large work function to ensure smooth hole injection into the organic layer.

Examples of materials forming the anode 110 include inorganic compounds and organic compounds. Inorganic compounds include, for example, metals (aluminium, gold, silver, nickel, palladium, chromium, vanadium, copper, zinc, etc.) or alloys thereof, metal oxides (indium oxide, tin oxide, indium-tin oxide ( (ITO), indium-zinc oxide (IZO), etc.), ZnO:Al or _SNO2 : A combination of metals and oxides such as Sb, metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesa glass, etc. You can. Organic compounds include, for example, polythiophenes such as poly(3-methylthiophene) and poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline. Conductive polymers, etc. can be mentioned. In addition, the material can be appropriately selected from materials used as anodes for organic electroluminescent devices.

The hole injection layer 120 serves to efficiently inject holes moving from the anode 110 into the light emitting layer 140 or the hole transport layer 130.

The hole transport layer 130 serves to efficiently transport holes injected from the anode 110 or holes injected from the anode 110 through the hole injection layer 120 to the light emitting layer 140. The hole injection layer 120 and the hole transport layer 130 are each formed by laminating or mixing one or two or more types of hole injection/transport materials or a mixture of a hole injection/transport material and a polymer binder. Additionally, an inorganic salt such as iron(III) chloride may be added to the hole injection/transport material to form a layer.

As a hole injection/transport material, it is desirable to have a high hole injection efficiency and to transport the injected holes efficiently. For this purpose, it is desirable to use a material that has a small ionization potential, a high hole mobility, and excellent stability, and in which impurities that become traps are unlikely to be generated during manufacture and use.

Materials forming the hole injection layer 120 and the hole transport layer 130 include compounds conventionally used as hole charge transport materials in photoconductive materials, p-type semiconductors, hole injection layers of organic electroluminescent devices, and Any compound can be selected and used among known compounds used in the hole transport layer.

These specific examples include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), and triarylamine derivatives. (Polymer having aromatic tertiary amino in the main or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3- Methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N, N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl- 1,1'-diamine, N ⁴ ,N ^{4 '} -diphenyl-N ⁴ ,N ^{4 '} -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]- 4,4'-diamine, N ⁴ ,N ⁴ ,N ^{4 '} ,N ^4' -tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4 Triphenylamine derivatives such as '-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene) -2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. In the polymer system, polycarbonate, styrene derivatives, and polyvinylcarboxylic compounds having the above-mentioned monomer in the side chain. Bazol, polysilane, etc. are preferred, but there is no particular limitation as long as it is a compound that forms a thin film necessary for manufacturing a light emitting device, can inject holes from the anode, and can transport holes.

Additionally, it is known that the conductivity of organic semiconductors is strongly influenced by their doping. This organic semiconductor matrix material is composed of a compound with good electron donating properties or a compound with good electron accepting properties. For doping of electron-donating materials, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) are used. It is known (e.g., “M.Pfeiffer, A.Beyer, T.Fritz, K.Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)” and “J.Blochwitz , M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)). These generate so-called holes by an electron transfer process in an electron-donating base material (hole transport material). Depending on the number and mobility of holes, the conductivity of the base material changes significantly. As matrix materials with hole transport properties, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) are known (Japanese Patent Publication, 2005) -167175 Gazette).

An additional hole buffer layer may be provided between the hole injection layer 120 and the hole transport layer 130, and may include hole injection or transport materials known in the art.

The light-emitting layer 140 is a layer that emits light by recombining holes injected from the anode 110 and electrons injected from the cathode 170 between electrodes to which an electric field is applied. The material forming the light-emitting layer 140 may be any compound (luminescent compound) that is excited and emits light by recombination of holes and electrons, and can form a stable thin film shape and have strong luminescence (fluorescence) efficiency in the solid state. It is preferable that it is a visible compound.

The light emission mechanism of the light emitting layer 140 is divided into fluorescence and phosphorescence. Fluorescence is a mechanism in which excitons in the singlet state, among excitons created by the combination of holes and electrons, descend to the ground state and emit light, while phosphorescence is a mechanism in which excitons in the triplet state descend to the ground state and emit light. By combining holes and electrons, 25% of singlet excitons and 75% of triplet excitons are generated. Unlike fluorescence, where only 25% of singlet excitons contribute to light emission, in the case of phosphorescence, 75% of triplet excitons and 75% of triplet excitons are generated. Since all 25% of singlet excitons that can be converted to triplet excitons through intersystem transition contribute to light emission, it is theoretically possible to achieve 100% internal quantum efficiency.

The light emitting layer 140 may be a single layer or multiple layers, and may include a host and a dopant to improve color purity and quantum efficiency. In the light emitting layer 140 of this structure, excitons generated in the host transfer to dopants and emit light. The host material and the dopant material may be of one type or a combination of multiple types. The dopant material may be contained entirely or partially in the host material. As a doping method, it can be formed by co-deposition with a host material, but may be deposited simultaneously after pre-mixing with the host material, or may be deposited by pre-mixing with the host material with an organic solvent and then forming into a film by a wet film forming method.

The amount of host material used varies depending on the type of host material, and can be determined according to the characteristics of the host material. The standard for the usage amount of the host material is 50 to 99.999% by weight, 80 to 99.95% by weight, or 90 to 99.9% by weight of the total light emitting layer material.

The amount of dopant material used varies depending on the type of dopant material, and can be determined according to the characteristics of the dopant material. The standard for the usage amount of the dopant material is 0.001 to 50% by weight, 0.05 to 20% by weight, or 0.1 to 10% by weight of the total material for the light emitting layer. The above range is preferable because, for example, concentration quenching phenomenon can be prevented.

Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.

When the emitting layer emits red light, the dopants include PIQIr(acac)(bis(1-phenylsoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), and PQIr(tris(1-phenylquinoline)iridium). , phosphorescent materials such as octaethylporphyrin platinum (PtOEP) or fluorescent materials such as tris(8-hydroxyquinolino)aluminum (Alq3) may be used, but are not limited to these. If the emitting layer emits green light, a phosphor such as Ir(ppy)3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the dopant. , but is not limited to this. If the light-emitting layer emits blue light, the light-emitting dopant may be a phosphorescent material such as (4,6-F2ppy)2Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), or PFO. Fluorescent materials such as polymers and PPV-based polymers may be used, but are not limited to these.

For example, as a blue light-emitting dopant, a polycyclic aromatic compound represented by the following formula (BD-YX2) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (BD-YX2) may be used.

In the above formula (BD-YX2), ring A, ring B, and ring C are each independently an aryl ring or heteroaryl ring, and at least one hydrogen in these rings may be substituted,

Y1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of Si-R and Ge-R is aryl, alkyl or cycloalkyl,

X1 _and It is optionally alkyl or optionally substituted cycloalkyl, and R in >C(-R) ₂ is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and the above >NR At least one of R and >C(-R) ₂ of R may be bonded to at least one of the A ring, B ring, and C ring by a linking group or single bond,

At least one hydrogen in the compound or structure represented by the formula (BD-YX2) may be substituted with deuterium, cyano, or halogen,

In the compound or structure represented by the formula (BD-YX2), at least one of A ring, B ring, C ring, aryl, and heteroaryl may be condensed with at least one cycloalkane, and At least one hydrogen may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-.

In particular, in the formula (BD-YX2), the aryl ring or heteroaryl ring as the A ring, B ring, and C ring is a 5-membered ring that shares a bond with the condensed 2-ring structure in the center of the formula consisting of Y1, It is preferable that it is a 6-membered ring.

The electron injection layer 160 serves to efficiently inject electrons moving from the cathode 170 into the light emitting layer 140 or the electron transport layer 150.

The electron transport layer 150 serves to efficiently transport electrons injected from the cathode 170 or electrons injected from the cathode 170 through the electron injection layer 160 to the light emitting layer 140. A suitable material for the electron transport layer 150 is a compound that has electron acceptor properties and has high mobility for electrons. In addition, it must have a LUMO (Lowest Unoccupied Molecular Orbital) energy level suitable for injecting electrons into the light-emitting layer 140, and the HOMO of the light-emitting layer 140 is required to prevent holes from flowing from the light-emitting layer 140 to the electron transport layer 150. (Highest Occupied Molecular Orbital) It is desirable to have a large difference from the energy level.

The electron transport layer 150 and the electron injection layer 160 are formed by laminating and mixing one or two or more types of electron transport/injection materials, respectively.

The electron injection/transport layer, which performs the functions of both the electron injection layer and the electron transport layer, is a layer that promotes the injection of electrons from the cathode and transports electrons to the light emitting layer 140, and has high electron injection efficiency, It is desirable to transport the injected electrons efficiently. For this purpose, it is desirable to use a material that has high electron affinity, high electron mobility, excellent stability, and that impurities that become traps are unlikely to be generated during production and use. The electron injection/transport layer in this embodiment may have the function of a layer that can efficiently prevent the movement of holes.

Materials forming the electron transport layer 150 or the electron injection layer 160 include compounds conventionally used as electron transport compounds in photoconductive materials, and known compounds used in the electron injection layer and electron transport layer of organic electroluminescent devices. It can be used by arbitrarily selecting from among the compounds. In the present invention, the compound represented by Formula 1 can be used as the electron transport material and/or electron injection material.

In general, the material used for the electron transport layer 150 or the electron injection layer 160 is a compound made of an aromatic ring or heteroaromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus. , pyrrole derivatives, condensed ring derivatives thereof, and metal complexes having electron-accepting nitrogen. Specifically, condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives such as 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide derivatives. , quinone derivatives such as anthraquinone and diphenoquinone, phosphorus derivatives, carbazole derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complex, azomethine complex, tropolone metal complex, flavonol metal complex, and benzoquinoline metal complex. These materials can be used alone, but may also be mixed with other materials.

Additionally, specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, and diphenylquinone. Derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N- (naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of auxin derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazoles Compounds, gallium complex, pyrazole derivative, perfluorinated phenylene derivative, triazine derivative, pyrazine derivative, benzoquinoline derivative (2,2'-bis(benzo[h]quinolin-2-yl)-9,9' -spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzoimidazole derivatives (tris(N-phenylbenzoimidazol-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives , oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(2,2':6'2"-terpyridinyl))benzene, etc.), naphthyridine derivatives ( bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, bistyryl derivatives, etc. I can hear it.

Additionally, a metal complex having an electron-accepting nitrogen can also be used, for example, a quinolinol-based metal complex, a hydroxyazole complex such as a hydroxyphenyloxazole complex, an azomethine complex, a tropolone metal complex, or a flavonol metal complex. and benzoquinoline metal complexes.

The above-mentioned materials can be used alone, but may also be used in combination with other materials.

Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, Phenanthroline derivatives and quinolinol-based metal complexes are preferred.

The electron transport layer or electron injection layer may also contain a material capable of reducing the material forming the electron transport layer or electron injection layer. A variety of reducing substances are used as long as they have a certain reducing property. For example, alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metals. At least one selected from the group consisting of halides, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals can be preferably used.

Preferred reducing substances include alkali metals such as Li (work function 2.3 eV), Na (work function 2.36 eV), K (work function 2.28 eV), Rb (work function 2.16 eV), or Cs (work function 1.95 eV). Examples include alkaline earth metals such as Ca (work function 2.9 eV), Sr (work function 2.0-2.5 eV), or Ba (work function 2.52 eV), and those with a work function of 2.9 eV or less are particularly preferable. Among these, more preferable reducing substances are alkali metals of K, Rb or Cs, more preferably Rb or Cs, and most preferable is Cs. These alkali metals have a particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL device can be improved and its lifespan can be improved. In addition, as a reducing material with a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, especially a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or Cs and A combination of Na and K is preferred. By including Cs, the reducing ability can be efficiently exerted, and by adding it to the material forming the electron transport layer or the electron injection layer, the luminance of the organic EL device can be improved and its lifespan can be improved.

Additionally, other preferred reducing substances include organometallic compounds represented by the following structural formula.

Among the structural formulas above,

Ar ₆ is hydrogen; heavy hydrogen; halogen group; Nitrile group; nitro group; hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

The curve represents the bonds and 2 or 3 atoms required to form a 5- or 6-membered ring with M, said atoms being substituted or unsubstituted by one or more substituents identical to the definition of Ar ₆ ;

M is an alkali metal or alkaline earth metal.

More preferably, M is an alkali metal selected from lithium, sodium, potassium, rubidium and cesium, and even more preferably M is lithium. For example, the reducing organometallic compound represented by the above structural formula is unsubstituted lithium quinolinate.

The above-mentioned reducing material may be used as a mixture or composition within one layer with the material forming the electron transport layer or electron injection layer, or may be used by forming a separate layer continuous with the electron transport layer or electron injection layer.

The cathode 170 serves to inject electrons into the light emitting layer 140 through the electron injection layer 160 and the electron transport layer 150.

The material forming the cathode 170 is preferably a material with a small work function so that electrons can be efficiently injected into the organic layer. Specific examples of cathode materials include metals such as tin, indium, calcium, aluminum, silver, lithium, sodium, potassium, titanium, yttrium, gadolinium, lead, cesium, and magnesium, or alloys thereof (magnesium-silver alloy, magnesium-indium alloy) , aluminum-lithium alloys such as lithium fluoride/aluminum, etc.) are preferable. In order to improve device characteristics by increasing electron injection efficiency, alloys containing lithium, sodium, potassium, cesium, calcium, magnesium, or these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this problem, there is a known method of using a highly stable electrode by, for example, doping a trace amount of lithium, cesium, or magnesium into the organic layer. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used. However, it is not limited to these.

The organic material layer may further include an electron blocking layer (or hole transport auxiliary layer) between the hole transport layer 130 and the light emitting layer 140, and a hole blocking layer (or electron transport auxiliary layer) between the electron transport layer 150 and the light emitting layer 140. An auxiliary layer) may be further included.

The electron blocking layer and the hole blocking layer allow the excitons generated in the light-emitting layer 140 to diffuse into the electron transport layer 150 or the hole transport layer 130 adjacent to the light-emitting layer 140, or do not recombine in the light-emitting layer 140 and form a hole transport layer ( 130) or the electron transport layer 150, which is a layer that prevents electrons or holes from passing over. As a result, the number of excitons contributing to light emission in the light-emitting layer increases, improving the light-emitting efficiency of the device and lowering the driving voltage. In addition, by preventing irreversible decomposition reactions due to oxidation by diffusion of holes into the electron transport layer 150, which moves electrons through reduction (electron reception), the durability and stability of the device are improved and the lifespan of the device is efficiently increased. can be increased.

Materials known in the art can be used as the electron blocking layer or hole blocking layer, and the compound represented by Formula 1 of the present invention can preferably be used as a material for the hole blocking layer (or electron transport auxiliary layer).

The organic material layer may further include a light-emitting auxiliary layer (not shown) between the electron blocking layer and the light-emitting layer 140. The light-emitting auxiliary layer may serve to transport holes to the light-emitting layer 140 and adjust the thickness of the organic material layer. The light emitting auxiliary layer may be a hole transport material known in the art.

The organic electroluminescent device according to the present invention may further include a protective layer or a capping layer formed on at least one side of the anode 110 and the cathode 170 opposite to the organic layer.

The materials used for the above hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer can form each layer individually, but may be used as a polymer binder such as polyvinyl chloride, polycarbonate, polystyrene, or poly(N-vinylcarboxylic acid). Bazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS Used by dispersing with solvent-soluble resins such as resins and polyurethane resins, and curable resins such as phenol resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins. It is also possible to do so.

<Method for manufacturing organic electroluminescent device>

Each layer constituting the organic electroluminescent device is made by using the materials that must make up each layer using methods such as deposition, resistance heating deposition, electron beam deposition, sputtering, molecular stacking, printing, spin coating or casting, and coating methods. It can be manufactured by forming a thin film. There is no particular limitation on the film thickness of each layer formed in this way, and it can be set appropriately depending on the properties of the material, but is usually in the range of 2 nm to 5 μm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like. When thinning a film using a vapor deposition method, the deposition conditions vary depending on the type of material, the target crystal structure and association structure of the film, etc. Deposition conditions are generally heating temperature of the deposition crucible +50~+400℃, vacuum degree 10 ^-6 ~10 ^-3 Pa, deposition speed 0.01~50nm/sec, substrate temperature -150~+300℃, film thickness 2nm. It is desirable to set it appropriately in the range of ~5㎛.

Next, as an example of a method for manufacturing an organic electroluminescent device, a method for manufacturing an organic electroluminescent device composed of an anode/hole injection layer/hole transport layer/host material and a light emitting layer/electron transport layer/electron injection layer/cathode made of a dopant material is included. Explain about it.

After producing an anode by forming a thin film of an anode material by a vapor deposition method or the like on a suitable substrate, thin films of a hole injection layer and a hole transport layer are formed on this anode. A host material and a dopant material are co-deposited on this to form a thin film to form a light-emitting layer. An electron transport layer and an electron injection layer are formed on this light-emitting layer, and a thin film made of a cathode material is formed by a deposition method or the like to serve as a cathode. By doing so, the desired organic electroluminescent device is obtained. In addition, when manufacturing the organic electroluminescent device described above, it is also possible to reverse the manufacturing order and manufacture the cathode, electron injection layer, electron transport layer, light emitting layer, hole transport layer, hole injection layer, and anode in that order.

<Application examples of organic electroluminescent devices>

Additionally, the present invention can be applied to a display device equipped with an organic electroluminescent element, a lighting device equipped with an organic electroluminescent element, etc.

A display device or lighting device equipped with an organic electroluminescent element is manufactured by a known method, such as connecting such an organic electroluminescent element and a known driving device (for example, a drain electrode or source electrode of a thin film transistor) in this embodiment. It can be driven using known driving methods such as direct current driving, pulse driving, and alternating current driving, as appropriate.

Examples of the display device include panel displays such as a color flat panel display, and flexible displays such as a flexible color organic electroluminescence (EL) display (for example, Japanese Patent Application Laid-Open No. 10-335066, See Japanese Patent Laid-Open No. 2003-321546, Japanese Patent Laid-Open No. 2004-281706, etc.). Additionally, examples of display methods include matrix and/or segment methods. Additionally, the matrix display and segment display may coexist in the same panel.

In a matrix, pixels for display are arranged two-dimensionally, such as in a grid or mosaic, and characters or images are displayed as a set of pixels. The shape and size of the pixel are determined depending on the purpose. For example, for image and text display on PCs, monitors, and televisions, square pixels with a side of 300㎛ or less are usually used, and in the case of large displays such as display panels, pixels on the order of mm are used. do. In the case of monochrome display, pixels of the same color can be arranged, but in the case of color display, red, green, and blue pixels are displayed in a row. In this case, there are typically delta types and stripe types. The driving method for this matrix may be either a line-sequential driving method or an active matrix driving method. Line-sequential driving has the advantage of having a simple structure, but when considering operating characteristics, the active matrix is sometimes superior, so it also needs to be used differently depending on the application.

In the segment method (type), a pattern is formed to display predetermined information, and a defined area is emitted. Examples include time and temperature displays in digital clocks and thermometers, operating status displays in audio devices and electronic cookers, and panel displays in automobiles.

Examples of lighting devices include lighting devices such as indoor lighting, backlights of liquid crystal displays, etc. (e.g., Japanese Patent Application Laid-Open No. 2003-257621, Japanese Patent Application Laid-Open No. 2003-277741, Japanese Patents (See Public Notice No. 2004-119211, etc.). Backlights are mainly used to improve the visibility of display devices that do not emit light themselves, and are used in liquid crystal displays, clocks, audio devices, automobile panels, display boards, and signs. In particular, considering that it is difficult to reduce the thickness of a backlight for a liquid crystal display device, especially for a PC, where thinness is an issue, because the conventional method consists of a fluorescent lamp or a light guide plate, the backlight using the light emitting element according to the present embodiment is thin. , characterized by light weight.

<Example>

Hereinafter, the present invention will be described in more detail through examples, but the present invention is not limited to these.

[Synthesis example of compound 1]

In a 1L round bottom flask, 50g (218 mmol) of 6-chloro-9-phenanthrenol, 29.3g (240 mmol) of PBA, 8.9g (21mmol) of S-Phos, 2.45g (10 mmol) of Palladium(II)acetate, 89.2 Potassium phosphate. Add g (656 mmol). Add 350 ml of Toluene and 150 ml of water as a solvent and reflux and stir overnight. After confirming the reaction by TLC, the reaction is terminated and extracted with EA/water. After concentrating the organic layer, it was subjected to silica column to obtain 45 g of Intermediate 1-1 (yield 76%).

Add 45 g (166 mmol) of Intermediate 1-1 and 450 ml of DMF to a 1L round bottom flask and stir. Slowly add 32.6 g (183 mmol) of NBS. Stir at room temperature for 3 hours. Check the reaction by TLC. After the reaction is completed, water is added to stop the reaction, and then filtered. The solid was adsorbed on silica and purified by column to obtain 50 g of Intermediate 1-2 (yield 86%).

In a 1L round bottom flask, 50 g (143 mmol) of intermediate 1-2, 54.5 g (215 mmol) of Bis(pinacolato)diboron, 5.2 g (7.2 mmol) of [1,1'-Bis(diphenylphosphino) ferrocene]dichloropalladium, and potassium acetate 28.1 Add g (286 mmol). Add 500ml of 1,4-dioxane as a solvent and stir under reflux overnight. After confirming the reaction by TLC, cool to room temperature. Extracted with EA/water, concentrated the organic layer, and subjected to silica column to obtain 43 g (yield 75.8%) of Intermediate 1-3.

In a 1L round bottom flask, 39 g (98 mmol) of intermediate 1-3, 22 g (82 mmol) of 2-Chloro-4,6-diphenyl-1,3,5-triazine, and 1.9 g (1.6 g) of Tetrakis(triphenylphosphine)palladium(0) mmol), add 22.7g (164 mmol) of potassium carbonate. Add toluene (154 ml) and water (66 ml) as solvents and reflux and stir overnight. After confirming the reaction by TLC, cool to room temperature. Extracted with EA/water, concentrated the organic layer, and subjected to silica column to obtain 29 g (yield 70.3%) of Intermediate 1-4.

After purging nitrogen into a 1L 3-neck round bottom flask, add 29g (57.8 mmol) of Intermediate 1-4, 11.7g (115 mmol) of Triethylamine, and 370ml of MC and cool to 0 degrees Celsius. Slowly add 18.2 g (86 mmol) of trifluoroacetic anhydride dropwise. Raise the temperature to room temperature and stir for 3 hours. After confirming the reaction with TLC, when the reaction is complete, lower the temperature to 0 degrees Celsius and slowly add water to stop the reaction. Extracted with MC/water, concentrated the organic layer, and subjected to silica column to obtain 30g of Intermediate 1-5 (yield 82%).

Add 30 g (47 mmol) of intermediate 1-5, 9.7 g (115 mmol) of 2-NBA, 1.09 g (0.9 mmol) of Tetrakis(triphenylphosphine)palladium(0), and 13 g (95 mmol) of potassium carbonate to a 1L round bottom flask. Add toluene (210ml) and water (90ml) as solvents and reflux and stir overnight. After confirming the reaction by TLC, lower the temperature to room temperature. Add MeOH to precipitate and filter. The solid is hot filtered through toluene. After concentrating the filtrate, it was recrystallized 5 times with toluene/acetone to obtain 8.7 g of Compound 1.

[Synthesis example of compound 71]

In the synthesis method of Compound 1, 7.3 g of Compound 71 was prepared using D5-PBA instead of 2-NBA.

[Synthesis example of compound 172]

In the method for preparing intermediate 1-1, 1-NBA was used instead of PBA to synthesize intermediate 2-1.

In the method for synthesizing intermediate 1-2, intermediate 2-2 was synthesized using intermediate 2-1 instead of intermediate 1-1.

In the method for synthesizing intermediate 1-3, intermediate 2-2 was used instead of intermediate 1-2 to synthesize intermediate 2-3.

In the method for synthesizing intermediate 1-4, intermediates 2-3 and 2-([1,1'-biphenyl]-4 are used instead of intermediates 1-3 and 2-Chloro-4,6-diphenyl-1,3,5-triazine Intermediate 2-4 was synthesized using -yl)-4-chloro-6-phenyl-1,3,5-triazine.

In the method for synthesizing intermediate 1-5, intermediate 2-4 was used instead of intermediate 1-4 to synthesize intermediate 2-5.

Compound 172 was synthesized using Intermediate 2-5 instead of Intermediate 1-5 in the method for synthesizing Compound 1.

[Synthesis example of compound 206]

In the synthesis method of compound 1, 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3 is used instead of 1-NBA. Compound 206 was synthesized using ,5-triazine.

[Synthesis example of compound 266]

In the method for synthesizing intermediate 1-4, intermediate 1-2 was used instead of intermediate 1-3, and 1-NBA was used instead of 2-Chloro-4,6-diphenyl-1,3,5-triazine to synthesize intermediate 5-1. .

In the method for synthesizing intermediate 1-5, intermediate 5-2 was synthesized using intermediate 5-1 instead of intermediate 1-4.

Method for synthesis of compound 1: Use intermediate 5-2 instead of intermediate 1-5, and 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-) instead of 1-NBA. Compound 266 was synthesized using dioxaborolan-2-yl)phenyl)-1,3,5-triazine.

[Synthesis example of compound 280]

In the method for synthesizing intermediate 1-4, intermediate 2-2 is used instead of intermediate 1-3, and 2-NBA is used instead of 2-Chloro-4,6-diphenyl-1,3,5-triazine to produce intermediate 6-1. was synthesized

In the method for synthesizing intermediate 1-5, intermediate 6-2 was synthesized using intermediate 6-1 instead of intermediate 1-4.

In the method for making compound 1, intermediate 6-2 was used instead of intermediate 1-5, and 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-[4-( Compound 280 was synthesized using 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine.

[Synthesis example of compound 331]

In the method for preparing intermediate 1-1, intermediate 7-1 was synthesized using dibenzo[b,d]furan-4-ylboronic acid instead of PBA.

In the method for synthesizing intermediate 1-2, intermediate 7-2 was synthesized using intermediate 7-1 instead of intermediate 1-1.

In the method for synthesizing intermediate 1-4, intermediate 7-2 is used instead of intermediate 1-3, and 1-NBA is used instead of 2-Chloro-4,6-diphenyl-1,3,5-triazine to produce intermediate 7-3. was synthesized.

In the method for synthesizing intermediate 1-5, intermediate 7-4 was synthesized using intermediate 7-3 instead of intermediate 1-4.

In the method for making compound 1, intermediate 7-4 was used instead of intermediate 1-5, and 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2) was used instead of 1-NBA. Compound 331 was synthesized using -dioxaborolan-2-yl)phenyl)-1,3,5-triazine.

By appropriately changing the raw material compounds, other compounds of the present invention can be synthesized by a method similar to the above-described synthesis example.

[Example 1]

Among the compounds synthesized in the synthesis example, the compounds in Table 1 below were purified by high purity by sublimation according to a conventional method, and then a blue organic electroluminescent device was manufactured as follows.

First, a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,500 Å was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaning the substrate using UV for 5 minutes and vacuum cleaning. The substrate was transferred to the vapor deposition machine.

On the ITO transparent electrode prepared as above, anode (ITO) / hole injection layer (100Å, compound HT and HAT-CN at a weight ratio of 97:3) / hole transport layer (1350Å, compound HT) / electron blocking layer (50Å, compound) HT-2) / Emitting layer (190Å, 97:3 weight ratio of compounds BH and BD) / Hole blocking layer (50Å, ET-2) / Electron transport layer (300Å, 50:50 weight ratio of compound 1 and LIQ) / Electron injection An organic electroluminescent device was manufactured by forming a layer (10 Å, Yb) / cathode (100 Å, weight ratio of magnesium and silver of 10:1) / capture layer (800 Å, compound CPL).

The structure of the compound used here is as follows.

[Examples 2 to 19]

The experiment was conducted in the same manner as in Example 1, except that the compound in Table 1 was used instead of Compound 1 as the electron transport layer.

[Comparative Examples 1 to 3]

The same experiment was performed in Example 1, except that Alq3 and compounds A and B were used instead of Compound 1 as the electron transport layer.

The results of measuring the emission characteristics of the organic electroluminescent devices manufactured according to Examples 1 to 19 and Comparative Examples 1 to 3 are shown in Table 1.

As can be seen from the measurement results in Table 1, the organic electroluminescent device using the compound of the present invention as an electron transport layer has a lower driving voltage and higher current efficiency than the organic electroluminescent device of the comparative example, and in particular, the device lifespan is longer. You can tell it’s excellent.

100 substrate
110 Anode (first electrode)
120 hole injection layer
130 Hole transport layer
140 light emitting layer
150 electron transport layer
160 electron injection layer
170 cathode (second electrode)

Claims (9)

A compound represented by the following formula (1);

In Formula 1,
Ar ₁ is deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group , a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, a substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, a substituted or unsubstituted Is selected from the group consisting of a C ₁ -C ₃₀ alkylsilyl group, a substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group,
L ₁ to L ₃ are the same or different from each other, and each independently represents a single bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₃ -C ₃₀ heteroarylene group,
R ₁ is deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group , a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, a substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, a substituted or unsubstituted Selected from the group consisting of a C ₁ -C ₃₀ alkylsilyl group, a substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group, and a plurality of R ₁ may combine with adjacent groups to form a substituted or unsubstituted ring,
o is an integer from 0 to 7,
A and B are the same or different from each other, and are each independently deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted substituted C ₃ -C ₂₀ aralkyl group, substituted or unsubstituted C ₆ -C ₃₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₃ -C ₂₀ A heteroaralkyl group, a substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, a substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and a substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group. is selected from the group consisting of
A can be bonded to L ₂ or B by a single bond, and B can be bonded to L ₁ or A by a single bond,
m and n are each integers from 0 to 2, and m + n ≥ 1,
At least one A or B is represented by the formula 2 below,

In Formula 2 above,
Het is a C ₃ -C ₃₀ heteroaryl group containing N as a heteroatom,
L ₄ is a single bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₃ -C ₃₀ heteroarylene group. According to paragraph 1,
A compound wherein at least one of Het of Formula 1 is represented by any one of Formulas 3 to 6 below;

In formulas 3 to 6,
A ₁ to A ₃₂ are the same or different from each other, are each independently N or CR ₂ , and are at least one of A ₁ to A ₆ , at least one of A ₇ to A ₁₄ , at least one of A ₁₅ to A ₂₄ , or A ₂₅ to A ₃₂ , at least one is N,
R ₂ of CR ₂ as A ₁ to A ₃₂ are the same or different from each other, and are each independently hydrogen, deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkyl group of C ₁ -C ₂₀ , a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted C ₃ -C ₂₀ aralkyl group, substituted or unsubstituted C ₆ -C ₃₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, Substituted or unsubstituted C ₃ -C ₂₀ heteroaralkyl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and substituted or unsubstituted is selected from the group consisting of C ₃ -C ₃₀ heteroarylsilyl groups, and adjacent R ₂ groups may be bonded to each other to form a substituted or unsubstituted ring,
Y ₁ is O, S or CR ₃ ,
R ₃ of CR 3 as Y ₁ is hydrogen, deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy _group , substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₃ -C ₃₀ Cycloalkyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ heteroalkyl group, substituted or unsubstituted aralkyl group of C ₃ -C ₂₀ , substituted or unsubstituted C ₆ -C ₃₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₃ -C ₂₀ Heteroaralkyl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and substituted or unsubstituted C ₃ -C ₃₀ heteroarylsilyl group. It is selected from the group consisting of, and adjacent R ₃ may be bonded to each other to form a substituted or unsubstituted ring. According to paragraph 1,
Ar ₁ of Formula 1 is a nitro group, a halogen group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, or a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted C ₆ -C ₃₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₃ -C ₃₀ aralkyl group, substituted or unsubstituted A compound characterized in that it is selected from the group consisting of a ringed C ₃ -C ₂₀ heteroaralkyl group. a first electrode,
a second electrode opposite the first electrode;
Comprising an organic material layer formed between the first electrode and the second electrode,
The organic material layer portion includes one or more organic material layers, and the organic material layer includes the compound of any one of claims 1 to 3. According to paragraph 4,
The first electrode is an anode,
The second electrode is a cathode,
The organic layer,
i) luminescent layer,
ii) a hole transport region interposed between the first electrode and the light emitting layer and including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; and
iii) interposed between the light-emitting layer and the second electrode, and comprising an electron transport region including at least one of a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection/transport layer,
wherein the electron transport region includes the compound,
Organic electroluminescent device. According to clause 5,
An organic electroluminescent device wherein the electron transport layer or the hole blocking layer includes the compound. According to clause 5,
Any one of the electron transport layer, the electron injection layer, or the electron injection/transport layer is made of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, or an alkaline earth metal. An organic electroluminescent element containing at least one selected from the group consisting of a halide, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal. According to clause 5,
An organic electroluminescent device in which any one of the electron transport layer, the electron injection layer, or the electron injection/transport layer includes an organometallic compound represented by the following formula (7);

Of the above formula 7,
Ar ₆ is hydrogen; heavy hydrogen; halogen group; Nitrile group; nitro group; hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
The curve represents the bonds and 2 or 3 atoms required to form a 5- or 6-membered ring with M, said atoms being substituted or unsubstituted by one or more substituents identical to the definition of Ar ₆ ;
M is an alkali metal or alkaline earth metal. A display device comprising the organic electroluminescent device of claim 4, wherein a first electrode of the organic electroluminescent device is electrically connected to a source electrode or a drain electrode of a thin film transistor.